How much is a ticket from Chicago Midway to Regina?

Depending on when you travel and how far in advance you book, fares between Chicago and Regina can differ a lot.

Choose a date to explore the best fares now.

If you’re flexible with timing, consider overnight flights — they often cost less and are less crowded. Exploring multiple date and time combinations can help you find the cheapest solution.

Which airports are most convenient between Chicago and Regina?

Whether it’s cost or connection time, the right airport combination can make a difference.

• Airports in Chicago: There are 3 airports in Chicago - Midway, O'Hare, Rockford.
• Airports in Regina: Regina is the only functioning airport for now.

In some cases, flying into a secondary airport can also reduce transfer costs. Connections from multiple airports give you more flight options and airlines.

Find the best flight from Chicago Midway to Regina

With Jetcost, you can filter results by flight time, airline, price range, and layovers. Choose direct or connecting flights, round-trip or one-way, and compare offers from Delta, American, United, and more.

Other popular destinations

Searching for flights to Canada? Travelers also looked at: Calgary, Edmonton, Montreal, Toronto, Vancouver.

Use filters to exclude options that don’t match your budget or travel preferences and personalize your search for Chicago Midway – Regina flights.